UA45383C2 - Кумаринохінолонкарбонові кислоти та спосіб їх одержання - Google Patents
Кумаринохінолонкарбонові кислоти та спосіб їх одержання Download PDFInfo
- Publication number
- UA45383C2 UA45383C2 UA97073970A UA97073970A UA45383C2 UA 45383 C2 UA45383 C2 UA 45383C2 UA 97073970 A UA97073970 A UA 97073970A UA 97073970 A UA97073970 A UA 97073970A UA 45383 C2 UA45383 C2 UA 45383C2
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- UA
- Ukraine
- Prior art keywords
- general formula
- compound
- differs
- снмн
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 150000004653 carbonic acids Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000000259 anti-tumor effect Effects 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
- 101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- -1 carboxyquinoloncoumaric acids Chemical class 0.000 abstract description 4
- 230000031018 biological processes and functions Effects 0.000 abstract description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- 230000012010 growth Effects 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 208000016063 arterial thoracic outlet syndrome Diseases 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010023825 Laryngeal cancer Diseases 0.000 description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 206010023841 laryngeal neoplasm Diseases 0.000 description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 201000002528 pancreatic cancer Diseases 0.000 description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DQGMASZUGMDEFA-UHFFFAOYSA-N 1-methyl-2-nitrosoimidazole Chemical compound CN1C=CN=C1N=O DQGMASZUGMDEFA-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000549366 Formicarius analis Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101000844611 Metallosphaera sedula (strain ATCC 51363 / DSM 5348 / JCM 9185 / NBRC 15509 / TH2) DNA-binding protein 7 Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002900 effect on cell Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Это изобретение касается новых кумаринохинолонкарбоновых кислот, у которых пиридоновая система находится в 3,4-, 6,7- и 7,8- позициях кумариновой системы и которые имеют общую формулу І , где R1R2=-NHCH=C(CO2R6)CO-, R3=NO2 или NH2, R4=R5=H, R6=H или C2H5; R1R2=-NHCH=C(CO2R6)CO-, R3=R4=H, R5=F, R6=H или C2H5; R1R2=-CO(CO2R6)C=CHNH=, R3=R4=R5=H, R6=H или C2H5; R1R2=R3=R4=-NHCH=C(CO2R6)CO-, R5=H, R6=H или C2H5; R1=H, или OH, R4=R5=H, R3=R4=-NHCH=C(CO2R6)CO-, R6=H или C2H5; R1=OH, R2=R3=H, R4R5=-CO(CO2R6)C=CHNH=-, R6=H или C2H5; R1=R5=H, R2=CH3, или СF3, R3R4=-C(CO2R6)C=-CHNH=, R6=H или C2H5, а также их фармацевтически приемлемых солей. Предмет изобретения также составляют процессы выработки новых кумаринохинолонкарбоновых кислот и их биологическое действие.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR960352A HRP960352A2 (en) | 1996-07-26 | 1996-07-26 | Novel coumarin quinoline carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA45383C2 true UA45383C2 (uk) | 2002-04-15 |
Family
ID=10946437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA97073970A UA45383C2 (uk) | 1996-07-26 | 1997-07-25 | Кумаринохінолонкарбонові кислоти та спосіб їх одержання |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5908933A (ru) |
| EP (1) | EP0820998B1 (ru) |
| JP (1) | JPH1087668A (ru) |
| CN (1) | CN1075500C (ru) |
| AT (1) | ATE205211T1 (ru) |
| BG (1) | BG63085B1 (ru) |
| CA (1) | CA2210448A1 (ru) |
| CZ (1) | CZ238297A3 (ru) |
| DE (1) | DE69706487T2 (ru) |
| ES (1) | ES2163694T3 (ru) |
| HR (1) | HRP960352A2 (ru) |
| HU (1) | HUP9701298A3 (ru) |
| PL (1) | PL321308A1 (ru) |
| PT (1) | PT820998E (ru) |
| RU (1) | RU2166504C2 (ru) |
| SI (1) | SI9700197B (ru) |
| SK (1) | SK101697A3 (ru) |
| UA (1) | UA45383C2 (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP960308A2 (en) * | 1996-07-02 | 1998-08-31 | Ljerka Poljak | New coumarine derivatives, process for the preparation thereof and their use |
| KR20010086166A (ko) * | 1999-01-13 | 2001-09-08 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | 케모카인 수용체 조절제로서의 관능화된 헤테로시클 |
| US6670391B2 (en) * | 2001-06-28 | 2003-12-30 | Dainippon Ink And Chemicals, Inc. | Benzopyran derivative and antiallergic agent |
| FR2827864B1 (fr) * | 2001-07-25 | 2005-09-16 | Servier Lab | Nouveaux derives de benzo[b]pyrano[3,2-h]acridin-7-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US8058427B2 (en) * | 2008-06-12 | 2011-11-15 | National Health Research Institutes | Coumarin compounds and their use for treating cancer |
| CN105218531B (zh) * | 2015-10-14 | 2018-03-16 | 西南大学 | 香豆素喹诺酮杂合体或其可药用盐及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060619A (en) * | 1976-01-14 | 1977-11-29 | Ayerst Mckenna And Harrison Ltd. | 1,4-Dihydro-4-oxo-benzothiopyrano (4,3-b)pyridine-2-carboxylates and derivatives |
| US4210758A (en) * | 1979-03-21 | 1980-07-01 | Warner-Lambert Company | 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamides |
| US4198511A (en) * | 1979-03-21 | 1980-04-15 | Warner-Lambert Company | 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-3-carboxamides and process thereof |
| GB9306062D0 (en) * | 1993-03-24 | 1993-05-12 | Lilly Industries Ltd | Pharmaceutical compounds |
| US5693647A (en) * | 1994-12-22 | 1997-12-02 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
-
1996
- 1996-07-26 HR HR960352A patent/HRP960352A2/hr not_active Application Discontinuation
-
1997
- 1997-07-18 US US08/897,057 patent/US5908933A/en not_active Expired - Fee Related
- 1997-07-23 SI SI9700197A patent/SI9700197B/sl unknown
- 1997-07-24 AT AT97112743T patent/ATE205211T1/de not_active IP Right Cessation
- 1997-07-24 JP JP9198505A patent/JPH1087668A/ja active Pending
- 1997-07-24 DE DE69706487T patent/DE69706487T2/de not_active Expired - Fee Related
- 1997-07-24 PT PT97112743T patent/PT820998E/pt unknown
- 1997-07-24 ES ES97112743T patent/ES2163694T3/es not_active Expired - Lifetime
- 1997-07-24 PL PL97321308A patent/PL321308A1/xx unknown
- 1997-07-24 SK SK1016-97A patent/SK101697A3/sk unknown
- 1997-07-24 EP EP97112743A patent/EP0820998B1/en not_active Expired - Lifetime
- 1997-07-24 CA CA002210448A patent/CA2210448A1/en not_active Abandoned
- 1997-07-25 HU HU9701298A patent/HUP9701298A3/hu unknown
- 1997-07-25 RU RU97113254/04A patent/RU2166504C2/ru active
- 1997-07-25 UA UA97073970A patent/UA45383C2/uk unknown
- 1997-07-25 BG BG101796A patent/BG63085B1/bg unknown
- 1997-07-25 CZ CZ972382A patent/CZ238297A3/cs unknown
- 1997-07-25 CN CN97117456A patent/CN1075500C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0820998A2 (en) | 1998-01-28 |
| HRP960352A2 (en) | 1998-08-31 |
| PL321308A1 (en) | 1998-02-02 |
| EP0820998A3 (en) | 1998-04-29 |
| JPH1087668A (ja) | 1998-04-07 |
| BG101796A (en) | 1998-10-30 |
| SK101697A3 (en) | 1998-05-06 |
| HUP9701298A2 (hu) | 1999-06-28 |
| HUP9701298A3 (en) | 1999-07-28 |
| EP0820998B1 (en) | 2001-09-05 |
| CN1176252A (zh) | 1998-03-18 |
| US5908933A (en) | 1999-06-01 |
| ATE205211T1 (de) | 2001-09-15 |
| SI9700197B (sl) | 2002-02-28 |
| CN1075500C (zh) | 2001-11-28 |
| DE69706487T2 (de) | 2002-05-08 |
| HU9701298D0 (en) | 1997-09-29 |
| CA2210448A1 (en) | 1998-01-26 |
| RU2166504C2 (ru) | 2001-05-10 |
| BG63085B1 (bg) | 2001-03-30 |
| CZ238297A3 (cs) | 1998-03-18 |
| SI9700197A (sl) | 1998-02-28 |
| ES2163694T3 (es) | 2002-02-01 |
| PT820998E (pt) | 2002-02-28 |
| DE69706487D1 (de) | 2001-10-11 |
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